No other jazz singer could get inside lyrics as evocatively as Billie Holiday. “Billie must have come from another world,” trumpet player Roy Eldridge once said, “because nobody had the effect on people she had. I’ve seen her make them cry and make them happy.” Even the famously demanding Miles Davis sang her praises: “She doesn’t need any horns. She sounds like one anyway.”

Lady Day—as tenor saxophonist Lester Young nicknamed her (he often dubbed a female musician “Lady”)—has been the subject of several books and an inauthentic movie (Lady Sings the Blues), but the life that became the music has never been so deeply revealed as it is in With Billie, a collection of more than 150 interviews with musicians, junkies, lovers, narcotics agents, relatives, and a decidedly heterogeneous group of friends. Linda Kuehl conducted many of the interviews in the 1970s, for a biography she didn’t live to complete. Now, Julia Blackburn, a novelist and biographer, has assembled and edited the transcripts, producing a portrait that’s both panoramic and intimate.

I knew Lady Day somewhat, and helped arrange her appearance on the historic 1957 CBS television program The Sound of Jazz, which is accurately and movingly described in the concluding chapter here. But With Billie helps me understand something Carmen McRae, a singer nurtured by Holiday, once told me: “Singing is the only place she can express herself the way she’d like to be all the time. The only time she’s at ease and at rest with herself is when she sings.”

Billie Holiday came up hard and was often hooked on drugs. And she had dreadful taste in men. “The kind of guys with big Cadillacs, big Packards or whatever, they represented something to Lady,” the comedian and tap dancer James “Stump” Cross says here. Of Lester Young, Cross notes, “He’d look at her—the look in his eyes when he played for her! He’d play his whole soul. But he wasn’t her type of man. He wasn’t manly.” Holiday fell for men who exploited her and left her alone even when she was with them. In rueful retrospect, she once remarked, “I was as strong, if not stronger, than any of them. And when it’s that way, you can’t blame anybody but yourself.”

Some of those men inhabit this book, but so do many witnesses to her resilience, her generosity, and, most important, her extraordinary musicianship. “She could find a groove wherever you put it,” says pianist Bobby Tucker, a longtime accompanist. “She could swing the hardest in any tempo, even if it was like a dirge. . . . Wherever it was, she could float on top of it.” Her clarinetist friend Tony Scott told me (and the quote is in the book), “When Ella [Fitzgerald] sings ‘My man he’s left me,’ you think the guy went down the street for a loaf of bread. But when Lady sings, you can see that guy going down the street. He’s got his bags packed and he ain’t never coming back.”

Offstage, Holiday could be very gentle, yet she also had a finely honed satiric wit. At the home of a mutual friend one night, I heard her precisely and saltily mimic a number of the more powerful booking agents and club owners in the business. Of the many illuminating recollections in With Billie, one that especially resonates with my memories is Bobby Tucker’s: “She didn’t like to see a small person being abused. She didn’t like to see their dignity squashed.”

At the end, in 1959, she was in Metropolitan Hospital in New York, suffering kidney failure and other ailments. Narcotics detectives, tipped that she had some drugs, arrested and fingerprinted her in bed. “They removed her record player, her records, the radio, and her comic books,” Blackburn writes. Denied bail, Holiday remained in the hospital. “Three policewomen kept a 24-hour guard at the door of her room.”

Lady Day died in that bed. She was 44. There was no money in her bank account, but when she left the world, she had a stack of $100 bills wrapped around her thigh with a garter belt.

During her last years, most jazz critics lamented what they judged the decline of her singing. Her voice cracked, and there wasn’t much of the spirited buoyancy of her early work. I differed with that appraisal in my reviews of Holiday’s 1950s recordings. Now I think that Benny Green, a British musician who became an astute critic, got it exactly right: “The trappings were stripped away, but where the process would normally leave only the husk of a fine reputation, it only exposed to view, once and for all, the true core of her art, the handling of a lyric. If the last recordings are approached with that fact in mind, they are seen to be, not the insufferable croaking of a woman already half dead, but recitatives whose dramatic intensity becomes unbearable—statements as frank and tragic as anything throughout the whole range of popular art.”

With Billie reveals where that intensity came from during Billie Holiday’s 44 years, and how singing gave her the strength to transcend at least some of the dark dissonances of her life. But it’s her classic recordings, including “Strange Fruit,” “Billie’s Blues,” and “God Bless the Child,” that reveal her the way she wanted to be remembered. She’ll continue to be remembered, and appreciated, for generations to come, by listeners who know nothing of the churning obbligato of her real life.

The most comprehensive collection of early Billie Holiday sessions is Lady Day: The Complete Billie Holiday, 1933–1940 (Columbia Legacy). The best introduction to the later recordings is The Billie Holiday Set: A Midsummer Night’s Jazz at Stratford ’57 (Baldwin Street Music), which includes several interviews with her.

Nat Hentoff is a columnist for The Village Voice. He is the author most recently of the essay collection American Music Is (2004).